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Chlorotriethylsilane, a colorless or slightly yellow transparent liquid with a pungent odor. CAS 994-30-9, EINECS 213-615-6, molecular formula C6H15ClSi. It usually has good solubility in organic solvents, but poor solubility in water. It is a non-polar molecule, which is related to the silicon atoms and ethyl groups in its molecular structure. Non polar molecules do not deflect in an electric field and are not easily soluble in polar solvents. It is a non electrolyte with low conductivity in aqueous solution. Conductivity is a measure of a substance's ability to conduct electricity, which is related to the concentration of free ions in the substance. An important organic synthesis raw material and intermediate that can be used to synthesize various organosilicon compounds. Can be used as a sealing agent for ethyl silicone oil and ethyl silicone rubber to improve product performance and stability. In certain chemical reactions, triethylchlorosilane can act as a catalyst or a component of a catalyst to promote the progress of the reaction. It can also be used in the fields of surfactants, defoamers, and as solvents or reaction media for certain chemical reactions.
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Chemical Formula |
C6H15ClSi |
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Exact Mass |
150 |
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Molecular Weight |
151 |
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m/z |
150 (100.0%), 152 (32.0%), 151 (6.5%), 151 (5.1%), 152 (3.3%), 153 (2.1%), 153 (1.6%), 154 (1.1%) |
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Elemental Analysis |
C, 47.81; H, 10.03; Cl, 23.52; Si, 18.63 |
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Synthesis of triethylchlorosilane: take chloroethane as raw material, copper as catalyst, and react with silicon powder at 350~370 ℃ to prepare a mixture of monoethyl trichlorosilane, diethyl dichlorosilane, triethylchlorosilane, ethyl dichlorosilane, and diethyl chlorosilane, which can be separated by using its boiling point difference.
Vapor and air form explosive mixture, explosive limit 0.7%~70.0% (volume).
Chlorotriethylsilane is an important organic silicon compound. Due to its unique chemical structure and reactivity, it is widely used in materials science, organic synthesis, and industrial fields. Its chemical properties can be summarized as follows:
Physical properties and basic characteristics
Chlorotriethylsilane appears as a transparent colorless to light yellow liquid at room temperature. It has a low density (0.89-0.90 g/mL) and a low boiling point (142-149°C), and is highly volatile. Its melting point is -50°C, indicating that it remains in a liquid state even at low temperatures. This compound is extremely sensitive to moisture and will react rapidly with water in the air to form hydrogen chloride and silanol compounds. Therefore, it needs to be stored under the protection of anhydrous and inert gases (such as nitrogen). Its refractive index (n²⁰/D) is 1.43, and the flash point is only 29°C. It is a flammable liquid and should be operated away from heat sources and high-temperature environments.
Chemical stability and reactivity
Hydrolysis sensitivity
The hydrolysis reaction of Chlorotriethylsilane is extremely rapid. When it comes into contact with water or compounds containing hydroxyl groups (such as alcohols), the Si-Cl bond breaks, generating triethyl silanol and hydrogen chloride. This characteristic makes it a typical representative of silaneating reagents and is often used to protect hydroxyl groups or introduce silicon-based groups. For example, in organic synthesis, it can be used through silaneation reactions to convert alcohols into siloxanes, enhancing the stability of the compounds.
Reactions with proton solvents
Apart from water, Chlorotriethylsilane also reacts with proton solvents such as methanol and ethanol, generating corresponding siloxanes and hydrogen chloride. Therefore, non-protonic solvents (such as dichloromethane, tetrahydrofuran) need to be used during storage and operation to avoid side reactions.
Thermal stability and decomposition
At high temperatures (such as the autoignition temperature of 280°C), Chlorotriethylsilane may decompose, releasing toxic gases (such as hydrogen chloride). Therefore, heating operations should be carried out in a fume hood and the temperature should be controlled.
Chemical behavior in catalytic and synthetic applications
Lewis acid catalyst
Chlorotriethylsilane can act as a weak Lewis acid, promoting certain organic reactions (such as condensation, cyclization) through the polarity of the Si-Cl bond. For example, in the formation of silicon-oxygen bonds, it can catalyze the dehydration condensation of silanol to generate polysiloxanes (the precursor of silicone rubber).
Silaneating reagent
One of its core applications is as a silaneating reagent, reacting with compounds containing active hydrogen (such as alcohols, phenols, amines) through the Si-Cl bond to generate stable siloxanes or silazanes. This reaction is used in drug synthesis to protect hydroxyl groups or in materials science to modify the surface of polymers.
Stability of derivatives
Compared with trimethylchlorosilane (TMSCl), the derivatives of Chlorotriethylsilane (such as triethyl siloxane) have higher stability against hydrolysis and are suitable for scenarios requiring long-term storage or complex reaction conditions.
Safety and toxicity
Acute toxicity
Chlorotriethylsilane is highly toxic and can enter the human body through inhalation, skin contact, or ingestion. Exposure can cause severe skin burns, eye damage, respiratory irritation, and even poisoning. When operating, protective gloves, goggles, and a respirator must be worn, and the operation should be carried out in a well-ventilated environment.
Environmental hazards
This compound is toxic to aquatic organisms and may cause long-term environmental impacts. Wastes need to be treated as hazardous chemicals and avoided direct discharge.
Emergency handling
If it comes into contact with the skin or eyes, it should be immediately rinsed with a large amount of water and medical assistance sought. In case of leakage, inert materials (such as sand) should be used to absorb it to avoid contact with water.
Key role in industry and research
Materials science
Chlorotriethylsilane is a key raw material for preparing silicone rubber, silicone resins, and silicone oil, catalyzing the formation of silicon-oxygen bonds to give materials with high-temperature resistance and chemical corrosion resistance.
Organic synthesis
In drug synthesis, it is used to protect hydroxyl groups or amines to prevent side reactions; in analytical chemistry, it can be used as a derivatization reagent to detect trace substances such as fluorides through gas chromatography.
Surface modification
By reacting with the hydroxyl groups on the surfaces of inorganic materials (such as glass, metal oxides), Chlorotriethylsilane can form silicon-oxygen bonds, enhancing the hydrophobicity or adhesion of the materials, and is widely used in coatings and adhesives.
Summary
Chlorotriethylsilane, due to its unique chemical properties - including high hydrolysis sensitivity, catalytic activity and silanization ability - has become a core compound in organic silicon chemistry. Its applications cover various fields such as material synthesis, drug protection and surface modification. However, during the operation, strict adherence to safety regulations is necessary to avoid toxic hazards. In the future, as the demand for environmentally friendly silane reagents increases, the development of derivatives of Chlorotriethylsilane and green synthesis processes will become the research focus.
1. Used for semi synthetic preparation of paclitaxel
Paclitaxel, also known as Taxol, is a taxane diterpenoid compound isolated from plants of the Taxus genus. It has a novel structure, unique anti-cancer mechanism, significant anti-cancer effect, and a wide anti-cancer spectrum, and is considered one of the anti-cancer drugs discovered so far.
CN201310430084.8 proposes a semi synthetic method for preparing paclitaxel, which has high reaction yield, mild reaction conditions, fast reaction time, fewer by-products, simple post-treatment, and is suitable for industrial production. To achieve this goal, the present invention adopts the following technical solution: a method for preparing paclitaxel, comprising the following steps:
(1) In the presence of CeCl3.7H2O, acetylate the 10th hydroxyl group of the compound shown (also known as 10-DAB) to obtain the compound shown in formula II (also known as Bacardine III);
(2) Protect the hydroxyl group at position 7 of the compound with triethylchlorosilane to obtain the compound shown in formula III (also known as 7-TES-Bakating III);
(3) The compound shown in formula IV (paclitaxel precursor) was obtained by condensation reaction with (4S, 5R) -2,4-diphenyl-4,5-dihydroxazole-5-carboxylic acid;
(4) Open the side chain oxazole ring of the compound and simultaneously remove the trichloroacetyl protecting group at position 7 to obtain paclitaxel.
2. Used for preparing a tear resistant cable sheath material
CN201610332792.1 provides a tear resistant cable sheath material with excellent flame retardant properties, as well as outstanding performance in tensile strength, elongation at break, fracture elongation retention after aging, and impact embrittlement temperature. The solution of the present invention is as follows: a tear resistant cable sheath material composed of the following weight parts of raw materials: 70-90 parts of polyvinyl chloride, 60-90 parts of ethylene vinyl acetate copolymer, 10-20 parts of 1-octene-ethylene polymer, 4-8 parts of octadecyl acrylate, 2-9 parts of triethylchlorosilane, 3-6 parts of diallyl isophthalate, 0.3-2.5 parts of sodium acetoacetate, 1-8 parts of diethanolamine stearate, 2-8 parts of N-cyclohexyl-2-benzothiazole sulfonamide, 1-5 parts of diethylene glycol ethylene ether, 0.6-3.8 parts of diethylene glycol dibutyl ether, 0.2-0.5 parts of tert butyldimethylchlorosilane, 1,6-dimethylchlorosilane. 1-7 parts of hexamethylenediamine, 3-6 parts of iron stearate, 1-5 parts of magnesium hydroxide, and 4-10 parts of carbon black. The anti tear cable sheath material of the present invention has excellent flame retardant properties, as well as excellent performance in tensile strength, elongation at break, fracture elongation retention after aging, and impact embrittlement temperature.
'tescl ', also known as Chlorotriethylsilane, is a type of organic silicon compound. Its CAS number is 994-30-9, and it is a commonly used reagent in chemical experiments. The purity is as high as 98%, ensuring its stability and reliability in chemical reactions. From a chemical structure perspective, the molecular formula is C6H15ClSi, and the molecular weight is 150.72. In addition, the compound has a login number of 213-615-6 in the EINECS database, providing convenient access and reference for researchers and industry. The physical properties are also very unique, with a density of 0.862 g/cm3, a melting point as low as -50 ℃, and a boiling point of 144.5 ℃ (760 mmHg). It is particularly important to note that it will decompose in water, so it is necessary to avoid contact with water during use and storage.
Taking the electronics industry as an example Tessl 'plays an important role in the preparation of silicone sealants. Organic silicone sealant has excellent high and low temperature resistance, electrical insulation performance, and chemical stability, and is widely used in the packaging and fixation of electronic components. During the preparation process, as one of the reactants, it reacts with other organic compounds to produce silicone sealant with specific properties. In addition, it is also commonly used in the construction industry to prepare coatings and adhesives.
These materials have excellent weather resistance, waterproofing, and bonding strength, providing strong support for the sustainable development of the construction industry. In the fields of medicine and pesticides, it also has a wide range of applications, providing strong support for the research and development of new drugs and pesticides. These practical cases fully demonstrate the important role and application value of 'tescl' or triethylchlorosilane in various fields.
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